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Reversal of Anomeric Selectivity with O ‐Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis
Author(s) -
Kumar Amit,
Schmidt Richard R.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200138
Subject(s) - chemistry , glycosyl , trimethylsilyl trifluoromethanesulfonate , anomer , boron trifluoride , catalysis , trimethylsilyl cyanide , trifluoromethanesulfonate , glycosylation , trimethylsilyl , base (topology) , combinatorial chemistry , organic chemistry , selectivity , medicinal chemistry , stereochemistry , biochemistry , mathematical analysis , mathematics
Boron trifluoride or trimethylsilyl trifluoromethanesulfonate catalysed the generation of thioglycosides from O ‐glucopyranosyl or O ‐galactopyranosyl trichloroacetimidates and thiols giving mainly or exclusively α‐thioglycosides. However, the same reactions with phenylboron difluoride as catalyst are highly β‐selective. An S N 2‐type reaction course under acid/base catalysis is invoked by these and previous results.